n. An organizational tool used by type-A personalities to plan every detail of a vacation or trip.

This is a reference to a Full House episode in which dad Danny uses his "clipboard of fun" to micromanage the family's vacation in Hawaii. It is often a derogatory term used when the rest of the group wants a more easy-going and less planned vacation.

"I think I'd enjoy this trip a lot more if Joe would leave the clipboard of fun back at the hotel"